


Bottoms Up

by awabubbles



Category: Supernatural
Genre: Anal Sex, Bottom Dean, Bottom Sam, Double Anal Penetration, Established Relationship, M/M, Sex Toys, Switching, references to topping for each brother
Language: English
Status: Completed
Published: 2016-12-06
Updated: 2016-12-06
Packaged: 2018-09-06 20:15:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,186
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8767603
Author URL: https://archiveofourown.org/users/awabubbles/pseuds/awabubbles
Summary: The brothers discover they both like to bottom. Dean comes up with a solution.[Thar be nsfw art inside]





	

 

It takes nine months for Sam to convince Dean that he should let his younger brother fuck him. Nine months after their first awkward hand-job exchange, and ten months after their first kiss. Dean has a brief existential crisis about taking dick up the ass which Sam has a hard time understanding. After all, if fucking your younger brother doesn't send you straight to hell in the first place, then switching things up every once in a while probably won't cause the apocalypse (again).  

Eventually Dean caves and decides to give it a try. That was a good night for Sam. A VERY good night. But afterwards his brother wouldn't _stop_  taking dick. Dean demanded he get fucked on every surface available, even in the bathroom bars after they hustle some sucker out of his money. It was a real goddamn turn on to see his brother on his knees begging for Sam’s cock. The only problem was it had been a full week-and-a-half since Sam _himself_ had gotten fucked, and, well, he sort of missed it. He missed being bent over the Impala, fucked so hard his cock slapped against the Kansas plates until he temporarily painted the idyllic skies a milky cream. Not that Dean crying for his little brother's cock wasn't hot and all, it was just seriously starting to cut into Sam’s whoring time. 

That’s why Sam starts to get nervous when Dean ruts up against him in their motel that night. His brother is hard and Sam’s cock tents in response, but the rest of his body is still tense with anticipation. The last few weeks they’ve been bickering like teenagers about who gets to bottom, making bets and challenging each other to ridiculous feats of endurance: the loser has to top. It’s stupid, and tiresome, and they haven’t been able to settle anything, so they just haven’t fucked. Which is heartbreaking really, and by the way Sam’s cock practically wants to explode from not being yanked on for more than 72 hours, it might be physically dangerous. But all Sam can think about is Dean’s cock in his ass, and he’s worried all Dean can think about is Sam’s cock in _his_ ass. It was blissfully tragic. Who knew their sex habits would suffer a bigger crises then 'we can't because we're brothers'?

“I think I have a solution,” Dean pants, humping his leg, lower lip red and swollen from where Sam had bit it. “To our, you know, _position_ problem.” 

“Oh?” Sam breathes, voice hitching a few octaves higher when Dean grabs his denim-clad cock and squeezes.

“Yeah,” Dean says, then lowers his eyes like he’s bashful which is funny cause his hand isn’t shy about asking for what it wants “Just um…hang on, fer a minute.” And then the pressure against Sam’s cock dissipates leaving him cold and wanting.

Dean digs around in his bag for a moment before recovering his mystery solution. He hesitates, shoots Sam another shy look, and then, finally, the reveal. Sam’s mouth drops open. He recognizes it instantly but he’s a little surprised to see about three feet of purple silicon in his brother’s hands. They've both turned into a couple of whores, haven't they?

“I saw it in this porno once,” Dean explains. “Squirt Gangbang, Volume Five. Of course those were all girls but I figure….the concept’s still the same.”

It’s a double dildo. Not like those dildos that women wear for their partners but like, one long schlong with two penis heads at each end. Sam grins at the sight of it. He imagines Dean jacking it to some anonymous porno, two blondes on top of each other, getting struck with inspiration while his orgasm grips him like the fist he's making around his dick.

It's sweet, and, kind of fucked up.

“So…how does it work?” he asks.

“We stuff each end into our asses,” is the response, as blunt as Sam should have expected. And when he rolls his eyes Dean adds quickly. “Whatever. We’ll figure it out, c’mere.” 

And that’s when Dean grabs him and throws him onto the bed. Sam bounces on his back, once, and doesn’t struggle as Dean begins to pull his jeans off, the dildo shoved between his teeth in order to free his hands; his big brother with a boner in his mouth. 

Once Sam’s dick is freed, Dean drops trou as well. Sam pulls his shirt off and moves back further onto the bed. He leans over the side and fishes into his own bag, pulling out a bottle of lube. They even have their own _lube_ preference now that their both cumsluts. Sam likes this brand called Slippery Stuff. He has to order it specially online, putting it into one of their cross-country PO boxes or their motel address when they actually stay in one town for a week. Dean on the other hand prefers the good old standby, Astroglide, because it's cheap and easy and that means you can slather on as much as you please. It’s too watery for Sam, dries out quicker than he’d like and it makes pushing inside that first time a little more difficult than it should be, but when it’s Dean’s turn to get fucked they use Astroglide; Sam’s, Slippery Stuff. 

Tonight, though, Dean doesn’t debate lube choice, he’s too eager to try their new toy. Instead, he accepts Sam's choice in lube graciously and crawls between his brother's legs. He lays the toy on the bed in front of Sam’s ass, and pulls Sam’s cheeks apart. “Little brother’s first,” Dean says hotly, and then dives in, face-first, right into Sam’s asshole.

Sam makes some kind of sound like a strangled animal. His asshole is finally getting the attention it needs and his dick is getting so excited it’s already drooling with anticipation. Dean eats out his asshole which, somehow, he’s gotten even _better_ at in his dabbling as a cumwhore. It makes Sam’s head spin and he hardly feels the first finger Dean inserts. Then, the next thing Sam knows, Dean’s grunting “yep you’re ready” and his asshole is feeling cold and empty once again.

Maybe Sam should feel embarrassed he can go from 0 to 60 but then again he doesn't want to waste much time either. He sits up to see Dean lathering their new lesbian sex toy with his lube and a mischievous grin. “Here we go, Sammy,” he says and then slowly inserts one end of the long purple super-dick inside of him.

“Unnngghhh!” Sam answers, when his brother asks if he likes it. It's slick, doesn't have too many ridges, is big but not TOO big, and yeah, yeah he feels pretty good. He's just not sure about the mechanics of this as his big brother asks Sam to hold the purple super-dick while he clambers onto the bed. Honestly, it takes some willpower not to fuck himself right there. But then  Dean straddles his hips and Sam figures if the dildo already has two dicks waving around, he might as well as wait for Dean to climb onto the other end.

“You don’t need me to…?” Sam proposes, as Dean quickly fingers his own asshole, leaning back for the toy in Sam’s hand.

“I uh…I’m good,” Dean says quietly. “I was um, preparing for this.” It’s that shyness again, mixed with a sort of self righteous smugness that makes Sam want to bend his brother over and fuck him senseless. And, thanks to this toy, Sam can now fuck Dean _and_ be fucked by Dean at the same time. He always knew his brother was a genius.

“Okay,” Dean says shakily, pressing the second end into his pre-prepped asshole. “Here we go.” 

Dean sinks down onto his end, and instantly Sam feels the cock in his own ass respond, tighten and bend like it’s suddenly alive. “Shit,” he gasps. Dean’s cock lays warmly against his belly, and yet, he’s still being stuffed full. “Shit, _fuck_.”

“S’good huh?” Dean says lazily, grinding down onto his end and gently fucking into Sam. “Now we can uh…both get what we want, huh?”

Sam chuckles and digs his fingers into Dean’s legs. “If I’d known what a cockwhore you were gonna become I wouldn’t have tried so hard to fuck you," he threatens.

“Shutup,” Dean grunts, and like he’s gonna prove his little brother wrong he works his hips a little more to fuck into Sam.

Sam grins, grinds upwards as well until they’re fucking each other, assholes being worked open, Dean's cock flopping lazily against Sam's belly.

“It’s hot, you know,” Sam assures. “You really let go when you get fucked. You’re just a little selfish about it, is all.”

“Got _this_ didn’t I?” Dean growls. And then he leans backwards. Grabbing the double dildo by the middle, he begins vigorously pumping the toy back and forth between them. It’s probably some dumb move his brother saw on Lesbo Gangbang Squirt The Revenge, or whatever, but damnit all if it doesn’t feel _good_.

“Fuck, Dean,” Sam pants, as his brother fucks them both. “Want you to fuck me with your fat double-cock, yes. Fuck, _yes_!” 

“ _Now_ who’s selfish,” Dean chides, but continues to ride. 

Their balls slap together as they work their hips in unison, as easy and effortless as the way they walk in unison. Sam wraps his hand around both of their cocks, feels himself close. But Dean isn't done with him yet.

"Not gonna crap out on me now are you?" his brother threatens. The dildo in his ass looses tension. Dean unmounts and flops down beside him. Sam is briefly dissapointed, until Dean starts pulling Sam ontop of him. "C'mon, get your ass up here," Dean insists, and Sam hastily crab walks onto his brother's lap. "There we go," Dean coaxes, "just like that."

Sam is propped ontop of Dean reverse cowgirl style, his legs shoved in the air and the double dildo half-hanging out of his ass. Dean leans forward and takes the other end, stuffing it back into his own ass, returning the tension Sam had enjoyed before. Then Dean pulls back Sam's thighs and pumps his hips. Sam, propped up on his arms, watches the purple dildo fuck into them both. It's way more of a turn on then Sam expected, seeing the same mega-dick push in and out of their asses.

"Jesus," Sam pants, feeling his brother's heavy cock brush his ass as they fuck each other. "I don't think I'm gonna last."

"You miss it that much?" Dean teases, but Sam's too far gone to care.

"Want you to come in my ass, though," Sam demands, practically begs. "Miss your cock inside of me."

"Think you can handle it?" Dean asks, and Sam's not sure what he means, thinks of course he's already being fucked on cock, Dean could swap them out. But when he feels Dean pressing his own cock into Sam, _alongside_ the dildo that's when he gasps, maybe a little too loudly, at two cocks inside of him. 

"Fuck, _oh fuck, Dean_ ," Sam moans.

"Gonna ruin that tight little hole of yours, Sammy," his brother threatens. "Gonna beg me to fuck you like this now." 

Dean is pushing his hips into him and it takes everything Sam has just to hang on. “Aaah!” he cries, as Dean’s hips stutter and jerk. “H-hurry,” he begs. “I-I’m almost-!” But Sam doesn't have to beg anymore. Dean orgasms, hard, pumping his little brother's ass full of cum.

"Now me," Dean pants, withdrawing, too soon for Sam's liking but he's close and he wants to pay his brother back in kind. He rolls off to one side and slides up behind his brother. He fingers Dean, hot and slick from the dildo inside him, and pushes himself inside of his bigger brother. 

"Sammy," Dean groans. "Fuck yeah, there's that monster dick." 

Sam grins, moving painfully slow because he's afraid he won't last. "That okay?" he asks.

"S'good," Dean assures. "Shit, fuck." The double dildo his still wrapped in Dean's hand. He brings it to his lips and sucks on the end that was inside of Sam, sucks on it and whimpers as Sam starts to fuck harder.

Sam wraps his arms around his brother, leans over his shoulder. Dean bends the dildo so Sam can reach, and he wraps his lips around the other end that was inside of Dean. Sam fucks his brother, and tastes him at the same time. He's delirious with pleasure. Holding his brother tight, Sam fucks as hard and as fast as he can until he comes violently inside of Dean, shaking, crying, and drooling over the dildo as his body releases one and half week's worth of repression inside the throbbing asshole of his bigger brother. 

Sam smiles lazily, satisfied and fucked senseless in every way he could have imagined. Dean had brilliantly solved their bottoming problem. Now they could both go back to their usual problems, like the monster of the week and pretending that they weren't a couple in public.


End file.
